CA2371931A1 - Steroid solution aerosol products with enhanced chemical stability - Google Patents
Steroid solution aerosol products with enhanced chemical stability Download PDFInfo
- Publication number
- CA2371931A1 CA2371931A1 CA002371931A CA2371931A CA2371931A1 CA 2371931 A1 CA2371931 A1 CA 2371931A1 CA 002371931 A CA002371931 A CA 002371931A CA 2371931 A CA2371931 A CA 2371931A CA 2371931 A1 CA2371931 A1 CA 2371931A1
- Authority
- CA
- Canada
- Prior art keywords
- product
- ketosteroid
- container
- coating
- metal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000443 aerosol Substances 0.000 title claims abstract description 47
- 150000003431 steroids Chemical class 0.000 title claims abstract description 32
- 239000000126 substance Substances 0.000 title claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 84
- 238000009472 formulation Methods 0.000 claims abstract description 74
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
- 238000002144 chemical decomposition reaction Methods 0.000 claims abstract description 19
- 229910052755 nonmetal Inorganic materials 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 95
- 238000000576 coating method Methods 0.000 claims description 42
- 239000011248 coating agent Substances 0.000 claims description 38
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 36
- 229960004436 budesonide Drugs 0.000 claims description 35
- 229910052751 metal Inorganic materials 0.000 claims description 33
- 239000002184 metal Substances 0.000 claims description 33
- 239000003380 propellant Substances 0.000 claims description 20
- 229910052782 aluminium Inorganic materials 0.000 claims description 18
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 18
- 229960002117 triamcinolone acetonide Drugs 0.000 claims description 18
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 claims description 18
- 229960003957 dexamethasone Drugs 0.000 claims description 15
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 239000011521 glass Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 229960000676 flunisolide Drugs 0.000 claims description 9
- 229910044991 metal oxide Inorganic materials 0.000 claims description 9
- 150000004706 metal oxides Chemical class 0.000 claims description 9
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 claims description 9
- -1 dexamethanone Chemical compound 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- SNHRLVCMMWUAJD-SUYDQAKGSA-N betamethasone valerate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(OC(=O)CCCC)[C@@]1(C)C[C@@H]2O SNHRLVCMMWUAJD-SUYDQAKGSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 6
- 239000005350 fused silica glass Substances 0.000 claims description 6
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 238000007740 vapor deposition Methods 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- OHYGPBKGZGRQKT-XGQKBEPLSA-N [(8s,9r,10s,11s,13s,14s,16s,17r)-9-chloro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(OC(=O)CC)[C@@]1(C)C[C@@H]2O OHYGPBKGZGRQKT-XGQKBEPLSA-N 0.000 claims description 4
- 239000004922 lacquer Substances 0.000 claims description 4
- 229940006003 beclomethasone 17-monopropionate Drugs 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
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- 230000003993 interaction Effects 0.000 claims description 3
- VHRSUDSXCMQTMA-PJHHCJLFSA-N 6alpha-methylprednisolone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)CO)CC[C@H]21 VHRSUDSXCMQTMA-PJHHCJLFSA-N 0.000 claims description 2
- MKPDWECBUAZOHP-AFYJWTTESA-N Paramethasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O MKPDWECBUAZOHP-AFYJWTTESA-N 0.000 claims description 2
- 229960000552 alclometasone Drugs 0.000 claims description 2
- FJXOGVLKCZQRDN-PHCHRAKRSA-N alclometasone Chemical compound C([C@H]1Cl)C2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O FJXOGVLKCZQRDN-PHCHRAKRSA-N 0.000 claims description 2
- 229940092705 beclomethasone Drugs 0.000 claims description 2
- 229960002537 betamethasone Drugs 0.000 claims description 2
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 claims description 2
- 229960002842 clobetasol Drugs 0.000 claims description 2
- CBGUOGMQLZIXBE-XGQKBEPLSA-N clobetasol propionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CBGUOGMQLZIXBE-XGQKBEPLSA-N 0.000 claims description 2
- 229960004299 clocortolone Drugs 0.000 claims description 2
- YMTMADLUXIRMGX-RFPWEZLHSA-N clocortolone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(Cl)[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)CO)[C@@]2(C)C[C@@H]1O YMTMADLUXIRMGX-RFPWEZLHSA-N 0.000 claims description 2
- WBGKWQHBNHJJPZ-LECWWXJVSA-N desonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O WBGKWQHBNHJJPZ-LECWWXJVSA-N 0.000 claims description 2
- 229960002593 desoximetasone Drugs 0.000 claims description 2
- VWVSBHGCDBMOOT-IIEHVVJPSA-N desoximetasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@@H]2O VWVSBHGCDBMOOT-IIEHVVJPSA-N 0.000 claims description 2
- 229960002344 dexamethasone sodium phosphate Drugs 0.000 claims description 2
- PLCQGRYPOISRTQ-FCJDYXGNSA-L dexamethasone sodium phosphate Chemical compound [Na+].[Na+].C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)COP([O-])([O-])=O)(O)[C@@]1(C)C[C@@H]2O PLCQGRYPOISRTQ-FCJDYXGNSA-L 0.000 claims description 2
- 229960004154 diflorasone Drugs 0.000 claims description 2
- WXURHACBFYSXBI-XHIJKXOTSA-N diflorasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O WXURHACBFYSXBI-XHIJKXOTSA-N 0.000 claims description 2
- 238000011049 filling Methods 0.000 claims description 2
- 229960003469 flumetasone Drugs 0.000 claims description 2
- WXURHACBFYSXBI-GQKYHHCASA-N flumethasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O WXURHACBFYSXBI-GQKYHHCASA-N 0.000 claims description 2
- 229960001347 fluocinolone acetonide Drugs 0.000 claims description 2
- FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 claims description 2
- 229960001048 fluorometholone Drugs 0.000 claims description 2
- FAOZLTXFLGPHNG-KNAQIMQKSA-N fluorometholone Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2(C)[C@@](O)(C(C)=O)CC[C@H]21 FAOZLTXFLGPHNG-KNAQIMQKSA-N 0.000 claims description 2
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- 229960002858 paramethasone Drugs 0.000 claims description 2
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- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 claims description 2
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 claims 1
- NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 claims 1
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- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000000063 preceeding effect Effects 0.000 claims 1
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- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 36
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 25
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- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/12—Aerosols; Foams
- A61K9/124—Aerosols; Foams characterised by the propellant
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D83/00—Containers or packages with special means for dispensing contents
- B65D83/14—Containers for dispensing liquid or semi-liquid contents by internal gaseous pressure, i.e. aerosol containers comprising propellant
- B65D83/38—Details of the container body
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D83/00—Containers or packages with special means for dispensing contents
- B65D83/14—Containers for dispensing liquid or semi-liquid contents by internal gaseous pressure, i.e. aerosol containers comprising propellant
- B65D83/44—Valves specially adapted for the discharge of contents; Regulating devices
- B65D83/52—Metering valves; Metering devices
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Mechanical Engineering (AREA)
- Pulmonology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13996199P | 1999-06-18 | 1999-06-18 | |
| US60/139,961 | 1999-06-18 | ||
| PCT/US2000/016462 WO2000078286A1 (en) | 1999-06-18 | 2000-06-15 | Steroid solution aerosol products with enhanced chemical stability |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2371931A1 true CA2371931A1 (en) | 2000-12-28 |
Family
ID=22489103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002371931A Abandoned CA2371931A1 (en) | 1999-06-18 | 2000-06-15 | Steroid solution aerosol products with enhanced chemical stability |
Country Status (8)
| Country | Link |
|---|---|
| US (4) | US6315985B1 (enExample) |
| EP (2) | EP1194121B1 (enExample) |
| JP (1) | JP4777560B2 (enExample) |
| AT (2) | ATE523190T1 (enExample) |
| AU (1) | AU777505B2 (enExample) |
| CA (1) | CA2371931A1 (enExample) |
| DE (1) | DE60026840T2 (enExample) |
| WO (1) | WO2000078286A1 (enExample) |
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|---|---|---|---|---|
| US20010031244A1 (en) * | 1997-06-13 | 2001-10-18 | Chiesi Farmaceutici S.P.A. | Pharmaceutical aerosol composition |
| DZ2947A1 (fr) * | 1998-11-25 | 2004-03-15 | Chiesi Farma Spa | Inhalateur à compteur de dose sous pression. |
| US6315985B1 (en) | 1999-06-18 | 2001-11-13 | 3M Innovative Properties Company | C-17/21 OH 20-ketosteroid solution aerosol products with enhanced chemical stability |
| IT1313553B1 (it) | 1999-07-23 | 2002-09-09 | Chiesi Farma Spa | Formulazioni ottimizzate costituite da soluzioni di steroidi dasomministrare per inalazione. |
| WO2001019342A2 (en) * | 1999-09-11 | 2001-03-22 | Glaxo Group Limited | Pharmaceutical formulation of fluticasone propionate |
| JP2003518484A (ja) * | 1999-12-24 | 2003-06-10 | グラクソ グループ リミテッド | サルメテロールおよびプロピオン酸フルチカゾンの医薬用エアゾル製剤 |
| IT1317846B1 (it) | 2000-02-22 | 2003-07-15 | Chiesi Farma Spa | Formulazioni contenenti un farmaco anticolinergico per il trattamentodella broncopneumopatia cronica ostruttiva. |
| IT1318514B1 (it) * | 2000-05-12 | 2003-08-27 | Chiesi Farma Spa | Formulazioni contenenti un farmaco glucocorticosteroide per iltrattamento di patologie broncopolmonari. |
| BR0015884A (pt) * | 2000-05-22 | 2003-07-08 | Chiesi Farma Spa | Formulações de soluções farmacêuticas estáveis para inaladores de dose medida pressurizados |
| TW523409B (en) * | 2000-09-15 | 2003-03-11 | Baxter Int | Container for inhalation anesthetic |
| US20040089293A1 (en) * | 2000-10-13 | 2004-05-13 | Paul Johnson | Medicament dispenser |
| GB0025092D0 (en) * | 2000-10-13 | 2000-11-29 | Glaxo Group Ltd | Medicament dispenser |
| US20020085978A1 (en) * | 2000-11-10 | 2002-07-04 | Mina Buenafe | Degradation-resistant glucocorticosteroid formulations |
| DE10062564A1 (de) * | 2000-12-15 | 2002-06-20 | Linde Ag | Schutzgas und Verfahren zum Lichtbogenschweißen |
| EP1241113A1 (en) | 2001-03-12 | 2002-09-18 | CHIESI FARMACEUTICI S.p.A. | Inhaler with means for improving chemical stability of medicinal aerosol solution contained therein |
| GB0106046D0 (en) * | 2001-03-12 | 2001-05-02 | Glaxo Group Ltd | Canister |
| ATE267591T1 (de) * | 2001-07-02 | 2004-06-15 | Chiesi Farma Spa | Optimierte tobramycin-formulierung zur aerosolbildung |
| GB0122725D0 (en) * | 2001-09-21 | 2001-11-14 | Glaxo Group Ltd | Drug dispensing components |
| EP1458354A1 (en) * | 2001-12-21 | 2004-09-22 | 3M Innovative Properties Company | Medicinal aerosol formulations comprising ion pair complexes |
| KR100947409B1 (ko) * | 2002-03-01 | 2010-03-12 | 키에시 파르마슈티시 엣스. 피. 에이. | 포모테롤 초미세 조성물 |
| US7344707B2 (en) * | 2002-05-15 | 2008-03-18 | The Procter & Gamble Company | Low combustion aerosol products in plastic packages having a reduced fire hazard classification that subsequently reduces storage costs |
| US20030215400A1 (en) * | 2002-05-15 | 2003-11-20 | The Procter & Gamble Company | Pressurized package made of a polyamide resin and containing dimethyl ether |
| JP3691459B2 (ja) * | 2002-06-14 | 2005-09-07 | 久光メディカル株式会社 | 粉末状吸入剤組成物 |
| ATE470468T1 (de) * | 2003-08-04 | 2010-06-15 | Alexza Pharmaceuticals Inc | Substrate für eine medikamentenverabreichungsvorrichtung und verfahren zur bereitung |
| AU2004266641A1 (en) | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Oxime substituted imidazo-containing compounds |
| EP1658076B1 (en) | 2003-08-27 | 2013-03-06 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| US20050054665A1 (en) | 2003-09-05 | 2005-03-10 | 3M Innovative Properties Company | Treatment for CD5+ B cell lymphoma |
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| ES2544477T3 (es) | 2003-10-03 | 2015-08-31 | 3M Innovative Properties Company | Imidazoquinolinas sustituidas con alcoxi |
| AR041873A1 (es) | 2003-10-30 | 2005-06-01 | Pablo Cassara Srl Lab | Una formulacion farmaceutica en aerosol adecuada para la inhalacion oral o nasal que contienen glucocorticoides en solucion estable al almacenamiento; un metodo para estabilzar formulaciones y uso de un agente estabilizante |
| US7897767B2 (en) | 2003-11-14 | 2011-03-01 | 3M Innovative Properties Company | Oxime substituted imidazoquinolines |
| JP2007511535A (ja) | 2003-11-14 | 2007-05-10 | スリーエム イノベイティブ プロパティズ カンパニー | ヒドロキシルアミン置換イミダゾ環化合物 |
| RU2409576C2 (ru) | 2003-11-25 | 2011-01-20 | 3М Инновейтив Пропертиз Компани | Системы, содержащие имидазольное кольцо с заместителями, и способы их получения |
| US20050121025A1 (en) | 2003-12-04 | 2005-06-09 | Gamard Stephan C.F. | Portable gas operating inhaler |
| WO2005066170A1 (en) | 2003-12-29 | 2005-07-21 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| CA2551399A1 (en) | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl, and imidazonaphthyridinyl sulfonamides |
| EP1595531A1 (en) | 2004-05-13 | 2005-11-16 | CHIESI FARMACEUTICI S.p.A. | Stable pharmaceutical solution formulations for pressurized metered dose inhalers |
| EP1730143A2 (en) | 2004-03-24 | 2006-12-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| WO2005123080A2 (en) | 2004-06-15 | 2005-12-29 | 3M Innovative Properties Company | Nitrogen-containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
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| US7943610B2 (en) | 2005-04-01 | 2011-05-17 | 3M Innovative Properties Company | Pyrazolopyridine-1,4-diamines and analogs thereof |
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-
2000
- 2000-06-13 US US09/592,885 patent/US6315985B1/en not_active Expired - Lifetime
- 2000-06-15 AU AU56142/00A patent/AU777505B2/en not_active Ceased
- 2000-06-15 AT AT06005429T patent/ATE523190T1/de not_active IP Right Cessation
- 2000-06-15 WO PCT/US2000/016462 patent/WO2000078286A1/en not_active Ceased
- 2000-06-15 EP EP00941435A patent/EP1194121B1/en not_active Expired - Lifetime
- 2000-06-15 AT AT00941435T patent/ATE320794T1/de not_active IP Right Cessation
- 2000-06-15 DE DE60026840T patent/DE60026840T2/de not_active Expired - Lifetime
- 2000-06-15 CA CA002371931A patent/CA2371931A1/en not_active Abandoned
- 2000-06-15 EP EP06005429A patent/EP1693053B1/en not_active Expired - Lifetime
- 2000-06-15 JP JP2001504351A patent/JP4777560B2/ja not_active Expired - Fee Related
-
2001
- 2001-10-04 US US09/970,746 patent/US6610273B2/en not_active Expired - Lifetime
-
2003
- 2003-07-30 US US10/630,414 patent/US20040033201A1/en not_active Abandoned
-
2005
- 2005-02-22 US US11/061,529 patent/US20050220717A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP1693053A3 (en) | 2007-06-27 |
| EP1693053A2 (en) | 2006-08-23 |
| AU5614200A (en) | 2001-01-09 |
| US20050220717A1 (en) | 2005-10-06 |
| ATE523190T1 (de) | 2011-09-15 |
| US20040033201A1 (en) | 2004-02-19 |
| DE60026840D1 (de) | 2006-05-11 |
| EP1693053B1 (en) | 2011-09-07 |
| US20020071810A1 (en) | 2002-06-13 |
| US6315985B1 (en) | 2001-11-13 |
| JP4777560B2 (ja) | 2011-09-21 |
| WO2000078286A1 (en) | 2000-12-28 |
| ATE320794T1 (de) | 2006-04-15 |
| JP2003502357A (ja) | 2003-01-21 |
| DE60026840T2 (de) | 2006-10-12 |
| US6610273B2 (en) | 2003-08-26 |
| EP1194121B1 (en) | 2006-03-22 |
| AU777505B2 (en) | 2004-10-21 |
| EP1194121A1 (en) | 2002-04-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |